


Alcohol and a Can-Do Attitude

by BlindSwandive



Series: Masquerade fills [3]
Category: Supernatural
Genre: Anal Fingering, And they're still not in love at the end, Brief references to scat, Fuck Or Die, Fuck-or-die but they're straight, M/M, Nonromantic sex, Prostate Massage, Slight internalized homophobia and gender roles, mentions of pegging, safe sex
Language: English
Status: Completed
Published: 2018-09-30
Updated: 2018-09-30
Packaged: 2019-07-20 15:25:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,686
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16140095
Author URL: https://archiveofourown.org/users/BlindSwandive/pseuds/BlindSwandive
Summary: Sam and Dean are hit with a fuck-each-other-or-die curse, so they handle it the way two straight, totally uninterested-in-each-other-sexually brothers would.





	Alcohol and a Can-Do Attitude

**Author's Note:**

  * For [TFWBT](https://archiveofourown.org/users/TFWBT/gifts).



> For the fabulous 2018 SPN Masquerade prompt: _Sam and Dean are familiar with fuck-or-die curses. They aren't interested in each other romantically, but have fucking each other down to an art. They get hit with a spell/curse/whatever and go about fucking each other the way two straight brothers would. Lots of bitching at each other, bickering, and mishaps. The more realistic, the better. Bonus if they take turns topping and bottoming and bitch at how the other does it._

The first time it happened, Sam was frankly just grateful that they’d figured out what they were facing on their own, without having called Bobby or anyone else who would be emotionally scarred by realizing what they were going to have to do to break the curse. It had practically had a big, red bow on it, the moldering witch on the floor cackling about their impending doom while her spellbook was _literally still open to the appropriate page._ It wasn’t like she’d exactly made it hard for them to avert their deaths. 

She’d even said something thrillingly clever like, “So what will it be—your lives or _your very souls?_ ” and Sam had rolled his eyes.

“Yeah, thanks, I think we’ll choose life.” Then he’d put a bullet in her brain. She hadn’t seemed to be expecting that, somehow.

When they’d got back to their motel and shucked off their gear, they’d dealt with it the way they dealt with most problems: alcohol and a can-do attitude.

Dean didn’t even bother with a glass, just sucked down a couple inches of bourbon from the bottle. “All right, Sammy, face down on the bed.”

“No fucking way, Dean. You get face down on the bed.”

“Excuse me,” Dean said with a glower, “I think I’ve got a better idea of what I’m doing here than you do, unless you had your lesbian fling in college like all the other girls.”

Sam’s face had twisted up sideways trying to figure that one out. “And what’s your experience, exactly?”

“On the bed, Sam,” Dean had insisted, apparently realizing he’d shared something he hadn’t meant to. Sam was _not_ going to let it go, not with his ass literally on the line.

“Seriously, Dean—what makes you think you’ve got a skillset I don’t here? Did you—oh my God, you _did_ service Oberon, didn’t you?” Oh, that was too good—Sam was going to be chewing on that one for material for years...

“Shut up,” Dean snapped, “I didn’t fucking service Oberon, I tried to murder everything that got close to me.”

Sam was peeling off clothing, but that didn’t mean Dean was getting away with this. “So spill. What was it, lost all your money in a bar bet and had to go ‘gay for pay?’ Or—dude, was it Cass?” he asked, with a little actual sympathy. “Some kind of Purgatory, foxhole thing? I’m not going to judge you, Dean,” he promised. And it was the truth; he wasn’t going to judge Dean for it at all. He just wasn’t going to let him live it down, either.

“Dude, I don’t—okay, look,” Dean bargained, “if I tell you, will you get on your damn knees, already?”

Sam paused to weigh that one. Ass rape by his brother, versus never knowing something he could cherish forever... 

“Fine,” Sam said, kicking off his underwear and climbing onto the bed. “But if this ever happens again, I’m going to be the one pitching.”

“Deal,” Dean said. Maybe he thought it was going to be a one-off. Little did he know.

“Okay, so. Lisa,” Dean said, stiffly, starting to drop clothing over a chair.

“Lisa,” Sam repeated, disbelieving.

“Yes. Lisa was—there were these pornos she liked, and you know me and porn—”

Sam laughed out loud, because that was an understatement.

Dean growled. “Do you want to hear this or not?”

Sam stifled, but barely. “Yeah, yeah. Go on.”

“So she liked these pornos, still had them on some old VHS tapes from the 90’s. Called _Bend Over Boyfriend._ ”

“Oh my God,” Sam muffled into his hand, trying not to bust up.

“Shut the fuck _up,_ Sammy.” The warning was palpable. “Unless you want me to use my superior knowledge for evil instead of good.”

That sobered Sam quickly. He pounded down a solid couple swigs of whiskey, hoping to undo it.

“That’s better,” Dean said, darkly, fishing in his bag. “She was really into these videos, and she—she had all the stuff,” he said, voice slightly strangled. “And what was I gonna’ do, say, ‘No, you turned your life upside-down for me and took me in off the street, but I won’t do this one little thing for you?’”

Sam tilted his head in a way he hoped conveyed that he understood that was fair.

“Plus,” Dean confided, “no one has sex like a yoga teacher. Pretty much if she and I got into it together, it was like a friggin’ hurricane, so I was pretty sure she’d make it worth my while, know what I mean?”

Sam kind of wished he didn’t, all of a sudden. Oh, well; the ship on staying fairly separated from his brother’s sex life had long since sailed, and any remaining separation was going to be obliterated any minute now.

“Oh, dude,” Dean said, interrupting his own story, “if you have to take a shit, you better go do it.”

Sam tried to look suitably disgusted by Dean’s crassness, but it had put a hook of paranoia in him. Wordlessly, he climbed back off the bed and headed for the bathroom, just to be very, very sure.

Through the door, Dean seemed to have an easier time talking about it, so that was something.

“Wash up while you’re in there, man,” he called, “don’t need to smell your toxic post-hunt swamp-ass.”

Sam was going to have to kill him, probably. “Get on with your story, Dean.”

“Fine, fine. So we watched these videos now and then when Ben was on trips or staying the night at a friend’s house, and eventually she springs it on me, how fun it’d be to try it out, and I’m saying, ‘Oh, sure, maybe,’ ‘cause I don’t think we can actually do anything about it without a trip to a sex shop, which you may have noticed are a little fewer and farther between in the Midwest than out in gay Stanford college towns.”

“Excuse me,” Sam interrupted, “how is it Stanford is gay when you’re the one playing bend-over-boyfriend in Indiana?”

“You’re playing... bend over... Indiana...” Dean mumbled weakly, but rallied. “Shut up. Anyway, I thought it would be like, I say yes, we have mind-blowing sex ‘cause she’s all turned on, and maybe in like a month or two we’ll get a chance to get to Indianapolis and maybe think about getting some toys, and maybe it won’t even happen at all.”

“Wrong,” Sam guessed.

“Wrong,” Dean confirmed. “Damned if she didn’t have the whole kit and kaboodle hiding in her nightstand the whole time.”

“So you wound up taking it in the ass that night?” Sam inferred.

“Yep. And a couple times a month after that,” he added, “when she was like, Idunno, ovulating or something and got all sex crazy. She’d just all of a sudden get this look in her eye over dinner and I’d know shit was about to get really interesting for a few days.”

“Man,” Sam said, impressed in spite of himself.

“Yeah,” Dean said, and Sam thought he could hear a smile in it through the door.

“You realize,” Sam added, because he couldn’t help himself, “you could have really easily lied and said Lisa was the one who liked taking it in the ass and you had to learn what you were doing for that.”

It sounded like a sneeze, through the door, but Sam was pretty sure it was Dean saying, “Sonofabitch,” as quiet as he could.

“Gesundheit,” he replied, anyway, and flushed.

Self-consciousness more than sensitivity to Dean’s wishes made Sam spend a couple of minutes with a washcloth and an irritatingly fragranced bar of motel soap by the sink. 

“Water’s hot if you want to wash up a little, too,” Sam hinted baldly when he emerged. He was toweling off his balls and his ass with a hand towel.

Dean appeared to be considering that. He looked down at his arm, as though he were wearing a watch (he wasn’t). After a few stray scratches over his wrist, he seemed to decide he could spare a minute for that. “All right, but we should probably get a move on, I’m starting to get open sores, here.”

Sam cursed and wished Dean hadn’t said that. He hadn’t noticed his own lesions opening up, and once he did, the urge to scratch was overwhelming. 

Still, if something was going up his ass, he’d rather it be clean. He scratched around the sores as carefully as he could to soothe the itch without making it worse. It half-worked.

Sam had poured and drunk a healthy shot of bourbon by the time Dean came out, damp and faintly floral, and that at least seemed to be numbing the itch a little. And the rising mortification. He suddenly wished he’d had some experience with this himself—any experience—but considering every other major life milestone Dean had been involved in, he guessed it wasn’t any worse it start here than with someone else. 

He changed his mind immediately. Of course it was worse. There was just jack he could do about it.

Sam sighed and abandoned his glass, rolling over onto his belly on the bed. He’d pulled down the comforter when the heavy-duty polyester felt like sandpaper on his sores, though the sheets weren’t exactly a luxury upgrade. “How do you want me?” he asked, finally.

“Just like that. But throw a couple pillows under your hips, make for an easier angle.”

Sam did, and almost looked back to figure out the nature of the sounds coming from behind him, but wasn’t sure he wanted to know.

“Hey, we still got that box of latex gloves we bought when you were being a pussy about cutting open corpses?”

“Dean, what if they'd died of something incredibly disgusting and infectious? I wasn’t being a pussy,” Sam protested. “I think they’re in the trunk somewhere. Or—you know I think I stuffed a pair in my bag, in that weird little inside pocket?”

“Awesome,” Dean said, cheerfully. “Won’t have to worry about trying to get the smell of your ass off me.”

Sam was almost insulted. “You’re going to use rubber gloves? Like I’m some kind of corpse?”

Dean’s eye-roll was audible. “Hygiene, Sam. Who has seen both volumes of _Bend Over Boyfriend,_ here, huh? And had the lecture from a health professional?”

“A yoga teacher is not a health professional,” Sam said, sourly.

“Dude, she had so much anatomy and bio training you would not believe it. They do like a thousand hours of studying and shit to get certified.”

“Not in ass sex, Dean,” Sam protested, but Dean grumbled him down.

“Jackpot,” he said after what sounded way too much like just turning Sam’s bag over and shaking it until everything fell out on the floor.

“Such a jerk,” Sam muttered, and tried to get comfortable. The pillows were crap, because that was motels for you. But, it had been a muggy, hot day, and there was something a little soothing, at least, about the forced air hitting the skin over his perineum where he was still just slightly damp. He let his hips loosen up a little, to expose his balls to the air, too. It was almost as good as scratching the sores would have been. 

“You’re in luck, Sam,” Dean said in a way that made Sam think he really, really wasn’t. “Even got the good shit, water-based. Hypoallergenic. In case your lily ass is as much of a delicate snowflake as the rest of you.”

Sam flipped him off, but didn’t even bother trying to look at what Dean was talking about. The distinct, liquid popping sound of a plastic bottle being tabbed open made it pretty clear, anyway.

“You got it for you,” Sam pointed out, “so it sounds like it’s your dick that’s ‘lily-ass.’”

Dean muttered unintelligibly, but then the bed dipped behind Sam and suddenly the wind went out of his Dean-harassment sails.

“You better be fucking careful,” Sam warned, and thought he had mostly suppressed the note of panic underlying it.

“Jesus, Sam, I will,” Dean said, exasperated. “I’m not an idiot. Doing this wrong could seriously fuck you up, okay? I’m not getting on top just for my own health, here.”

Sam blinked, and found he actually believed Dean, there. He rallied quickly, though. “You’re the one with experience taking it.”

“And you could seriously fuck _me_ up if you did it wrong,” Dean argued, and Sam didn’t actually have anything to say to that. He made a mental note to look up proper anal sex hygiene and etiquette procedures in case this came up again, and committed to paying very, very careful attention to what Dean did, here.

The lube hitting his hole felt frigid. “Jesus, Dean!” he yelped.

Dean, the fucker, laughed. “Sorry, sorry man. I’ll, uh, I’ll warm it up next time.”

Sam scowled against the mattress, folding his arms under his head and glaring daggers at the headboard.

“Okay, so first you want to try to relax as much as you can. If you clench, it’ll hurt.”

“Right, because telling someone to relax always makes that so much easier to do.”

“What, you want some fucking candles and a glass of wine, Princess?” Dean teased, and there was an unattractive squelching noise coming from behind Sam.

“You’re such a moron,” Sam sighed.

“Gonna’ start putting one finger in, okay?” Dean informed him, businesslike. “If you bear down like you’re trying to take a shit, it’ll actually go in easier.”

Sam thought that was an immensely gross thought, but when the not-as-cold tip of Dean’s finger nudged wet and slick against him, he tried it. It didn’t work, at first, because Sam had clenched shut automatically at the feel of ingress, but Dean said, almost kindly, “Relax, Sammy,” and Sam took in and released a long breath and managed to let go. When he pressed down with his muscles as instructed, Dean’s finger slid in over the first knuckle.

That felt—weird. Really, really weird. The urge to try to push him back out was great, because something lingering in the vestibule had always called for clearing house, up ‘til this point, but Dean was right, and trying to push him out just opened the way for Dean to swim upstream, so to speak. Sam thought absurdly of a salmon run and had to stifle a delirious laugh on his wrist.

“What?” Dean asked, and there was a note of paranoia. No one liked being laughed at in bed.

“Nothing,” Sam managed, “just—got a weird image. Not important.”

Dean, thankfully, didn’t pry.

“Let me know when you get used to it,” he plowed on, as though Sam weren’t getting ready to lose his mind over here. “Or more used to it, anyway—ideally you’d just hang out with something small in your ass for a while and try again with something bigger in a couple days, get the feel for it all, but we don’t got that kind of time.” There was a note of sincere apology hiding under that, and Sam felt a little surge of affection for his brother, however bizarre the circumstance.

“That’s sweet, Dean,” he said, unable to stop himself from a little good-natured mocking, even so.

Dean responded by shoving his finger the rest of the way up inside Sam, and Sam hissed, wondering if maybe baiting Dean right now wasn’t his best bet after all. His rectum felt like it was having some kind of seizure, clenching and unclenching at random and without conscious direction from Sam, and Dean’s finger felt hard as iron, inappropriate and hateful. It felt so wrong he had to clench his jaw against complaining.

“Relax, Sammy,” Dean said, again, and this time there was a note of pity. That was almost worse. “Try some deep breaths, okay? Slow in, slow out.”

Sam gritted his teeth and closed his eyes, trying it out. The stuttering muscles settled down, and Sam thought of skittish horses and stray dogs. Gentle them and soothe them and try not to get bit. He wondered if Dean was thinking of something similar.

“That’s it,” Dean encouraged, and Sam wished he wouldn’t. “Doin’ good, Sammy.”

“Can you shut up and get on with it, Dean?” Sam finally asked, desperately. 

Dean didn’t respond, thankfully. He planted one hand on one of Sam’s ass cheeks, pressing it out wide, and that felt weird, and gave Dean more room to work. He was slowly twisting his finger around and starting to slide it back and forth a little, and though the innate wrongness of something ungiving and unbending remained, the pain of it was diminishing slowly. When Sam clenched, it would flare up, but Dean always froze immediately when he did, so the sawing feeling of his knuckle rubbing against tight muscles never lasted more than a second. 

Sam would never admit it, but Dean was being surprisingly attentive and sensitive.

On second thought, maybe he would admit it, eventually. Some point when he needed to get Dean back for denigrating Sam’s masculinity and Sam needed some counter-evidence.

Eventually he sighed, a little bored but glad the strain was going down. Dean didn’t say anything when he withdrew his finger--and that felt weirdly awful, uncontrolled and dangerous, Sam suddenly paranoid he was about to shit all over the bed even though he’d just cleared himself out. If things weren’t supposed to go _up_ your ass, they really weren’t supposed to come out of it without your permission. It was an uncomfortably helpless feeling.

Dean broke radio silence to warn him briefly: “Two fingers,” and Sam braced, dutifully bearing down to make way. 

And if one finger felt wrong, two felt—well, no, not much wronger at all, actually. Sure, the intrusion was larger, and his fingers still definitely felt like they had bones inside them, but the feeling was more familiar, now, and Sam could survive it. He felt stretched impossibly wide, though, which wasn’t a good sign. 

Dean was trying to move his fingertips around, but didn’t seem to be getting much traction. Sam felt like a rubber band wrapped too many times, elastic but barely. Then something touched his perineum, brushed the backs of his balls, and that felt... okay, really good, actually, though that Sam for certain would never admit. Still, he focused on the sensation of sensitive nerves to distract him from the work of Dean’s fingers, and it actually took him a minute to realize when Dean had gotten a knuckle further inside.

Huh.

Sam tried to push himself open again, but his asshole was just going to have to be worked like C4 until it would soften enough to be molded, he figured. Dean was making some bizarre motion like rocks in a rock tumbler, and when it stopped hurting, there was actually something kind of nice about the full feeling at the opening, something a lot like the warm buzz of nerves over his taint. He guessed he shouldn’t be surprised by that; men had been taking it in the ass for a couple thousand years, at least, and there must be something that kept them coming back, apart from all-consuming devotion. Or pure masochism.

He supposed he could handle this.

“Did you like it?” Sam asked, and didn’t realize he was going to until it was out of his mouth.

“What?” Dean asked, freezing.

“Did you like it,” Sam repeated, “when Lisa did you like this?” It was honest curiosity. It must have shown, because Dean actually answered.

“Yeah, a little. Mostly it was fun how hot it got her, but, man,” he said, with feeling, sounding almost dazed, “when she really got going, she could take you apart. The prostate is your friend, Sam.”

Sam made a little sound of consideration, and something relaxed low in his back, and in his head. It felt like warm water was permeating his spine.

He could ignore the unspoken ‘so you might as well enjoy it.’ He didn’t need Dean hinting that at him. But privately, he thought, he might as well enjoy it.

Dean was falling back into the forbidden speech patterns. “Doin’ good, Sam, getting there.”

“Dean,” Sam warned, and Dean sighed.

“Whatever, man. You should be kissing my ass I’m taking my time with this, you could be in a world of hurt right now.”

“I am,” Sam reminded him, “since I’m the one with my brother trying to crawl up my ass. Oh,” he added, acidly, “and half my body has broken out in sores.”

Dean did something with his fingers that shut Sam up promptly. It felt like a little pulse missile going off right behind his balls, hot and nebulous and sharp somehow at once.

Okay, maybe _that_ was what people had been lining up for for the last few millennia.

Sam hadn’t been hard, up to this point, because gross, but now, for the first time, he could imagine at least not getting screwed out of an orgasm in this venture. He didn’t actually know if people could come just from getting rubbed on inside like that, but thought it might be like with girls and their g-spots, some yea and some nay. Oh, well; not like he couldn’t get some friction on his dick if he needed to.

The silence behind Sam got potent enough that it turned into that loud kind of silence you got when someone was trying very hard not to speak. Eventually it got just as oppressive as Dean’s nattering itself, so Sam asked, “What?” exasperation evident.

“You okay?” Dean asked, and his self-consciousness was palpable.

Sam took pity. “Yeah. Fine, Dean,” he said, and it came out sounding almost fond. He’d pretend that hadn’t happened.

“Good,” Dean breathed, relieved. “Think you want to try for one more, or get this show on the road?”

Sam debated that one internally. After a long moment, he ventured, “I guess—get as close to the size of your dick a you can, first, whatever that is.”

Dean withdrew about halfway, and there was another disgusting squelching sound, and an unholy amount of lube greased the way for a third finger.

Sam still felt like too-tight elastic, but it seemed to be going easier now. Bearing down worked again, at least, and Dean had added enough lube to let a submarine through, let alone a few fingers, so the ‘sticking’ feeling Sam hadn’t quite been able to put a name to was gone. He realized in its absence that he’d felt a little like an accordion, parts of him bunching up and pulling back rather than entirely letting Dean move around freely. It was a big improvement. 

“Why didn’t you add that much in the first place?” Sam asked, reproachfully.

“You seized up when it was cold,” Dean said, defensive. “You hurting?” he asked, though, and it was more concerned than accusatory.

“No,” Sam admitted reluctantly. “Still would have been nice to have things running this smoothly from the beginning.”

“I’ll remember that for next time,” Dean said, drily.

“Yeah, not happening.”

“Whatever,” Dean said, maddeningly knowingly.

Sam gritted his teeth. “Will you just get in there already? These sores are making me crazy. I think I’m starting to get one on my dick.”

Dean hissed in sympathy. “Yeah, shit, just a second. Why don’t you, uh... pretend to be a girl,” he said awkwardly, and Sam was honestly not sure if it was meant to be a joke or not. He ignored it, for safety’s sake.

There was the unmistakable sound of a condom opening, and Sam felt a strange sense of relief. Why he hadn’t just assumed there’d be at least the illusion of separation he didn’t know, but it was comforting, anyway. 

Dean pulling out his fingers was less comforting. He did it faster this time, and that had its benefits and drawbacks—the disconcerting loss-of-bowel-control feeling didn’t go on for as long, but it definitely grated Sam’s nerves a little raw. 

There was a wet, plastic kind of sound that repeated in rhythm. It was nice to know that Dean was having to work himself up to this, too; Sam shouldn’t be the only mortified one here.

“Deep breath, Sammy,” Dean said, and Sam couldn’t manage to bitch at him for it, because there was a sudden grip of panic in his chest. He did try to take a deep breath, and Dean was taking one, too, climbing up behind him on the bed. When Dean told him to bear down, again, he did without question, and then it was there, sliding in—forever, and ever, and ever—hot and hard but at least more yielding than Dean’s knuckles had been. 

“Hurry up,” Sam said, through a clenched jaw. He couldn’t keep bearing down much longer, and he just knew that as soon as he stopped he’d start clenching and that would be a bitch if Dean was still trying to get the rest of the way in.

Dean shushed him—honest to God shushed him like he was a little kid or an animal bent out of shape. 

“Damnit, don’t—don’t shush me, you dick, you’re sticking your—your dick up my ass, if I’m—then I’m going to—”

Sam’s coherence circled the drain and left entirely. He thought his eyes were crossing. Thank God Dean had used another copious handful of lube, for this.

After a year or two, Dean was seated flush, his hips up against Sam’s ass and their balls touching. Why that should be so much more upsetting than the actual penetration Sam couldn’t figure—something to do with intimacy, maybe—but he pulled a pillow over the top of his head for some semblance of privacy and safety and silently dared Dean to say one single word about it. There would be bloodshed. Lots.

Dean was mercifully silent, apart from panting like he was trying to hold up a building that was falling over. Sam mashed the pillow down over his ears to blot it out. _Think happy thoughts,_ he coached himself morbidly. Maybe if _he_ thought of Lisa back there, or some random girl whom he had neither gotten killed nor left horribly in the lurch, it would be less hideous. It didn’t turn out to be a promising train of thought. 

Sam tried to detach, to take the thing clinically and a step at a time. What had he wanted to do? Take notes? What had Dean done?

As his brother came down onto his elbows, weight just barely hovering off of Sam’s back, Sam started cataloguing what Dean had done right and what Sam would need to know how to do in future. Latex gloves; lots of lube; slow progression in size; massage of muscles. Stopping whenever Sam clenched, waiting to start moving until Sam had relaxed again. 

What had he done wrong? Talking too much; not enough lube in the fingering portion of the show; forgetting to keep attending to the happy special place Sam was pretty sure from Anat and Phys was his prostate, and a direct line of nerves right into his balls.

Eventually, Sam realized Dean was humping away with abandon, and Sam had gone almost half out of his body by getting distracted. When he came back into his skin and his nerves, he tried not to make any sudden movements or even realizations, afraid it would spur him to tighten down and be in a world of hurt. 

With careful mental probing, Sam found he was more or less not resisting Dean with his body at all, at this point. And while that seemed totally backwards, it was probably for the best, since Sam wasn’t really much of a masochist when it wasn’t necessary for the greater good, e.g. purging all-encompassing hallucinations of Hell and Lucifer, or saving the world. There was still something he might cautiously, privately admit was more than a little pleasurable in the way Dean’s rocking was rolling over all those sensitive little nerve endings near the edges, but it wasn’t enough to make his balls tighten up the way that little downward curl had.

Sam began drawing diagrams in his head. He factored in the usual upward curve of a penis, the apparent slight sway to the left Dean’s took in particular, the suspected location of the prostate, and the limits of flexibility and hip motility. He eventually concluded that Dean’s doggy-style arrangement was fatally flawed, and that something more approximating a supported missionary position or cowgirl would be much more effective at getting the receiving party off. There might be some hope for a back-to-front orientation (which did, granted, have the benefit of them not having to look one another in the eye) if the one taking it were more upright, or the pillows were under the waist instead of the hips; something that would bring the invading dick into a more perpendicular orientation relative to the spine of the receiver.

He was just about to tell Dean so when Dean came, sputtering, and collapsed on Sam’s back.

“You selfish fuck,” Sam scolded, from under the pillow, before he could consider whether that was actually a good idea. The sudden relief from the sores fading away into nothing was probably better than an orgasm, though, and he groaned in spite of his better efforts.

Dean just heaved long, slow breaths, slowly crushing the life out of Sam with his weight.

Sam scrambled to get the pillow off of his head, a task made trickier by Dean trying to use it to fall asleep on. He got a corner up enough that he could grind out, “Off,” forcefully enough to wake Dean from his apparent stupor.

“Can’t,” Dean muttered, wheezing. “Didn’t work.”

“Yes,” Sam contradicted, “it did, look at your skin.”

“Did,” Dean mumbled, “still got sores. More, now.”

Sam mulled that one over. The solution seemed pretty obvious to him.

***

“You be goddamn careful with that,” Dean was practically shouting, terror evident. “I’m not kidding, Sammy, we’re talking loaded guns, here, weapons of mass destruction.”

“I’m not going to shoot your ass, Dean,” Sam said, but it was hard not to laugh, for all he sympathized with Dean’s plight. Sam had just been in it, himself. But that didn’t mean he didn’t feel a little bit like payback was in order.

“You know what I mean,” Dean insisted, half-frantic.

“Just relax,” Sam said, with only a little vicious glee.

“And why the hell am I on my back, Sam?” Dean went on.

“You’ll see,” Sam said, sternly. “Now shut up and grab your knees.

***

Dean had the pillow over his face in less than a minute, probably to keep from spontaneously dying of embarrassment. 

“Bet you’re glad I’m such a ‘chick,’” Sam teased, while he worked his latex-covered fingers in and out of Dean. He didn’t have the same finesse Dean had had, if Dean was to be believed, but he was a quick study. “No way I’d have put a hand in there without legit medical protection,” he went on. 

He privately thought he should have cut his nails; they were short, but up against the quick would probably have been nicer on the other end. That was probably a big reason to use gloves. He wished he’d made Dean try to take a shit, too, though; he was pretty sure there was... residue on the glove, and the thought alone was so revolting Sam couldn’t look for more than a second at a time. 

Sam didn’t need to look very carefully to know whether he was doing his job well, though. Though Dean’s dick would forever be relegated to “the source of many of our problems” status, there was a kind of clinical satisfaction to be had in making it jump around in a way Sam’s most definitely had _not,_ when he’d been on the other end of this. Sam might not have the delicacy and dexterity Dean had shown, or the experience, or even quite as intuitive a grasp of when Dean’s muscles were starting to seize, but he clearly had the better strategic mind, and Dean was making ridiculous noises up into the pillow and sweating bullets. Dean had done better at keeping it from hurting, which Sam was going to be silently grateful for until he died, but Dean was probably having a much better time.

By the time Dean was cursing, actively and colorfully, Sam figured he could get on with it, and he peeled the glove off and inside-out with excruciating care, and denial about what was on the now hidden surface. The other benefit to having Dean on his back, pillows under his ass, of course, was that he wouldn’t need to make nearly as much incidental contact. He could crowd up against Dean’s pillows on his knees and touch him with little but his dick and a few careful fingertips.

Dean said something eloquent like “Fuck, fuck, fuck, fuck,” when Sam started easing his way in. He tried not to notice (or take too much satisfaction in) the fact that his dick was bigger than Dean’s. It confirmed a private suspicion, anyway.

On a trip into the city, a gay friend of Jess’s had told Sam very casually that Sam was getting so much attention from the men in the Castro because Sam had “big dick body”—he was tall with long, angular limbs, big paws, a long neck, and joints pushing out a bit at the seams. Sam had doubted him with the full force of his usual lack of self-confidence, but Jess (who had had significantly more experience than Sam, at that point) had agreed that Sam’s dick was definitely above average. Sam had a brief flash of dismay that he didn’t remember her friend’s name, anymore; everything from those years had gone a little thin and hazy with time and grief. He could remember clearly the way she’d loved his cock, though, feeling him up through his pants every chance she got and willingly—no, eagerly—giving him blowjobs. He could remember her trying to find new surfaces in their apartment that they hadn’t managed to have sex on yet, always managing to come up with some new place to christen when she really put her mind to it.

It was dangerous territory to think on, but he pictured her bent awkwardly over the edge of the bathtub one day, using the bathmat under her stomach for a cushion and lifting her ass in the air. He could still kind of see the skirt she’d been wearing at the time (light blue, snug, with some kind of pattern maybe?) and how it had looked when he’d slid his fingers up under it and hitched it over her hips. She hadn’t been wearing underwear and he’d fallen on her like some kind of half-mad caveman, pounding decidedly unenlightened possessiveness into her flesh like if he just fucked her hard enough she’d be his so far inside that she’d never leave.

If he could keep the image from spiraling out in time, Dean would get the benefit of that treatment. The usually-suppressed caveman part of Sam beat his chest at the thought of fucking Dean into submission, but he really, _really_ didn’t want to think about that. ‘Like wrestling,’ he thought desperately, ‘three pins or a submission.’ He could fuck his brother like he was fighting him. And if his mental schematics were on course, Dean would be a happy, gibbering mess by the end of it.

It took about three strokes to prove sufficiently that he’d worked out the right angle. Dean was shouting into his pillow, and it was not a sound of pain or protest.

No wonder Lisa liked doing this to him; Sam could see what Dean had meant about her taking him apart. Dean was boneless, flayed open and utterly soft and violently hot inside. There was a definite sensation of conquering, the satisfaction of success, even if Sam didn’t have the benefit of actually wanting to be up Dean’s ass. Dean did clench on him hard enough to hurt a couple of times—the sheer power in those muscles was insane, and Sam had been a little worried he’d wind up with broken fingers when he was working Dean open—but mostly he howled into the pillow, loose and giving and in no control of himself whatsoever. Sam felt more powerful than when he’d realized if he goosed Dean in the ribs just right he’d fly a foot into the air, yelping in a hilariously undignified way. It had taken the threat of broken fingers to stop Sam then, too.

The rush of power was going to Sam’s head, but he closed his eyes long enough to fix the more specifically _sexually_ gratifying image of Jess’s gorgeous body in his mind. Dean had already gotten off once, so if Sam didn’t get the job done for him again, that was Dean’s problem. Anyway, the curse only seemed to need Sam to get off in Dean for Dean to be relieved of oncoming death, so that was really the only job Sam had committed to. And if Dean having to throw himself into a cold, unsatisfying shower afterwards was a little hilarious to consider, Sam wouldn’t admit it even to himself.

 _Think happy thoughts,_ he thought again dizzily, and didn’t realize he was grinning.

The furnace of Dean’s ass stuttered on Sam again, and that was all Sam needed to tip over. He had to brace himself against a loss of balance, and accidentally used Dean’s hoisted knee for that, but he was upright again pretty quickly and drawing out, ignoring the way Dean berated him to go slow and careful, goddammit. Dean’s belly was streaked with precum; Sam was definitely not going to mention that. Not unless Dean really kept riding him about needing to take his time getting out.

The sight of Dean’s sores filling out, covering over, and finally vanishing was actually pretty fascinating, even if it meant Sam had to see his dick twitch (presumably as satisfied with the relief from pain and itching as Sam had been). Dean just rolling over onto his side and jerking it until he hit another orgasm, however, felt like an act of aggression, outright warfare.

“Dean!” he scolded in disbelief. “At least go into the damn bathroom!”

Dean ignored him, and polished it off in moments, sighing his relief. He wiped his hand off on the bed and dug himself out from under the pillow before staggering across the short space between the beds, collapsing on the clean one in clear indication he meant to sleep there.

“Dean,” Sam warned, “I am not sleeping in your jizz.”

Dean yawned, and either fell promptly into snoring sleep or faked it better than usual.

Sam muttered obscenities and went to grab a tissue to get the condom off without having to actually touch the outside. When he’d gotten it off and ‘accidentally’ failed to tie off the end, he dropped it onto Dean’s chosen bed, and followed that up with the other condom from the trash and both discarded gloves. Just see how much he liked his clean bed, then.

Sam stripped the fitted sheet off of what was going to be his bed, apparently, and pulled out the flat sheet to lie on. He went to pull the comforter up over him, but thought better of direct contact (he’d never really believed they washed those nearly as often as they implied they did). He dug something to sleep in out of the chaos that had been the contents of his bag spilled out on the floor and resented Dean actively for a minute, while he turned out the lights and climbed in. Dean would probably wake up wearing some of the contents of his own ass and Sam’s balls, though, so Sam was willing to be the bigger man and let bygones be bygones.

**Author's Note:**

> Yes, _Bend Over Boyfriend_ is real. They're billed as educational, which, yes. You can learn a lot from them.


End file.
